Dear Sammy
by An Eleanor Jane
Summary: When Dean dies in a hunt he leaves three letters, one for Sam, one for Jess and one for their child. "Even from beyond the grave, Dean had managed to fix his little brother once again." Mainly angst and fluff.
1. Jess's Letter

**Disclaimer: I do not won any of these beautiful characters, although I wish I did.**

 **This is an idea that been taking up space in my head for forever and I've finally got it down on paper.**

 **I will love you forever if you review, and I love criticism, I really want to improve the way I write.**

 **Enjoy!**

The letter arrived through the door of their apartment at 10:00pm on a Sunday night by a shadowy stranger that had disappeared by the time Jess had opened the door. It was in a crinkled brown envelope that was a bit crumpled around the edges. The name on it read _Sammy Winchester_ in a messy scrawl. The blonde frowned. It must be for Sam, but she couldn't remember anyone ever calling him Sammy before.

She walked into the kitchen, biting her lip at the scattered beer bottles next to the sink. Ever since they had heard the dreadful news her boyfriend just hadn't been the same. He had taken a couple of weeks off, and had taken to drinking too much and lying in bed for far too long. She was used to her boyfriend being happy, strong, cheerful and brave. But now he was a wreck. And it scared her, the emptiness and pain in his eyes.

It had been two months, and he was back in classes. But he moved like a zombie, progressing through the day an autopilot. Jess's friends had told her to leave him, that sometimes people just fell out of love and she should let him go. She had blankly refused. It seemed ridiculous to her to give up on the man that she loved because he was in pain. Give up on her boyfriend when he needed her? No chance.

He'd changed the night he'd got the call from the hospital telling him that a mountain lion attack had taken the life of his big brother.

The day Dean Winchester died, a part of Sam had too.

Jess had never got to meet Dean. She heard the stories though, and there were a lot of them. Their mother had died when Sam was still a baby, and their dad took them on he road. Dean, only four years older, pretty much raised his younger brother. According to Sam, Dean wasn't scared of anything apart from affection and losing the people he cared about. Leaving for Stanford and leaving his brother nearly tore Sam apart. When her boyfriend had too much to drink it was always his brother's name he murmured, and that was also the name he screamed when one of his brutal nightmares woke him up sweating.

"Sam?" She peered into the darkened bedroom, stepping inside and sitting down next to her boyfriend. He didn't respond, just stayed staring at a certain point on the wall. Tears slid down his face, dripping onto the law book lying open on his lap. She touched his arm hesitantly. "Sam, are you okay?" She regretted the words as soon as she uttered them. Of course he wasn't okay. He turned towards her, his eyes siding down to the envelope clutched in her hands. "This came in the post." His eyes widened. She gently placed it on his lap, sliding the tearstained book out from underneath it and placing it on the bedside table.

"That's Dean's writing." His voice sounded hollow and hoarse. He tore open the envelope, three smaller envelopes tumbling out. He picked up the biggest one, which said _Sammy_ on the front in the same messy scrawl. Sam put it next to him and read what the other two said. His eyebrows furrowed, before picking one up and handing it to Jess.

On the front was scrawled ' _For the girl (or boy) that Sammy decides to spend the rest of his life with'._

"Do you want to be alone when you read it? If you want me to be here…"

"Can I be alone? Please?" There was such begging in his voice she couldn't disobey.

"You want me to read it?" She said the words gently, as if he would break if she said it too loudly.

He nodded. "It's addressed to you, isn't it? I mean, you're the girl I want to spend the rest of my life with. If you'll have me." He sounded so sure of himself, of his love for her, she couldn't help but let her breath catch in her throat. The girl he wanted to spend the rest of his life with.

At that moment she knew she would never give up on him. She loved him, and he loved her, and together they would get through this.

"Of course. I love you."

"I love you too." She kissed him gently, and he kissed her back. He hadn't even opened the letters yet and already Dean's words were starting to heal him. She hugged him and stepped out of the room, leaving Sam to himself.

She ripped open the letter, suddenly nervous of what might be inside. She'd never met this Dean before, and he'd never met her. She knew she was being ridiculous, but she was terrified that she wasn't good enough for Sam, and Dean somehow knew. Dismissing her fears, she read the letter.

 _To the girl or boy Sam has decided to fall in love with,_

 _I_ _do_ _did a dangerous job, and I guess that got me killed in the end. When me and Sam were growing up, a lot of the time we only had each other. I want you to know, I'm sorry for hurting him by dying. I'm so sorry for leaving my little brother. But here's what I've learnt from dealing with the not so little brat all my life. I made bullet points because my hand's getting tired._

 _Sam blames himself for things that have nothing to do with him. Just keep telling him that it isn't his fault and maybe it'll get into that thick skull of his._

 _He also carries far too many books around with him, and gets a sore shoulder. It was from an injury when he was growing up, but an ice pack takes away the pain. He'll never complain that he's in pain, so you have to try and work it out._

 _DO NOT, and I repeat, DO NOT let him have the first shower. He will use all the hot water and spend about an hour in there._

 _I have disclosed a few photos of Sam when he was a little goofy kid, to use for blackmail at your leisure._

 _Force him to watch movies, because he's managed to get through his life without watching any actual good ones._

 _His music taste is horrible, and please tell him that at every possible moment._

 _When he wakes up from a nightmare the most comforting thing you can do is just be there for him, convince him that you're okay and that it was all just a dream._

 _And finally (and this is the important bit), don't let this ruin his life. Don't let my death do him any more damage. He's one of the strongest guys I know, but he might need someone to hold him together through it._

 _That's about it. I hope the two of you will both be very happy, and it's a shame I never got to meet you. Unless I did get to meet you between now and the time of my death, in which case, it was lovely to meet you._

 ** _Dean Winchester_**

 _P.S. Please force him to get a haircut._

Jess wiped away the tears hastily away from her eyes. From what she could tell Dean loved Sam to death, and considering the way Sam talked about him the feeling weren't one way.

"I promise I'll do everything I can." She whispered into the air, blinking away more tears. "I promise."

She got herself a glass of water, folding the paper up carefully. She would be good enough for Sam. She had to be.


	2. Sam's Letter

**Here's part two! I hope you enjoy it. I loved the reviews, they were so sweet.**

 **Disclaimer: I don't own these characters, but I do own a very creative imagination.**

Sam Winchester sat on his bed, his hands balled at his sides, staring down at the envelope.

Dean was dead. His big brother was dead. It was so typical Dean to think about Sam first, himself second. Somehow he knew that this was Dean last letter, the one he'd arranged to send to Sam after he died. Tying up the loose ends.

Sam closed his eyes and breathed heavily. He opened the letter, and his breath caught in his throat when he saw the oh-so-familiar writing. That writing, which had appeared on ever report card and trip letter, on every Christmas card and scrawled message. His heart ached when he saw it.

 _Dear Sammy,_

 _First of all, I'm sorry. If you're reading this it means I'm dead, and if I'm dead it means you're hurting, so I'm sorry. You know I'm not much of a writer, but I'm laid up in hospital after a nasty werewolf attack with a broken leg, so I thought I'd write to you._

 _There's a retired hunter in California who owes me a favour, so I'm going to pass these to him to give to you when I die. And if his heart stops beating before mine, you'll never read this at all._

 _You know in that song by Kansas, Carry On My Wayward Son? Listen to that. It'll save me writing a massive soppy letter straight out of a chick flick about how you shouldn't just give up and all that._

 _This is what I want you to do. Go to school. Do lawyery stuff. Find a girl (or guy) that makes you happy. Get a house with a white picket fence. Get a dog. Call the dog Colin. Don't forget the salt lines. Do all the stuff that makes you happy, and enjoy yourself. You always were the smart one, so go and be great._

 _I'm not asking you to forget me. Cause if it was the other way around there was no way in hell I would forget you. What I am asking is for you to give me five minutes every day. Listen to a Led Zep song, take a drive in the Impala, drink some whisky, do something that reminds you of me. I want a good five minutes when you think about us growing up, when we took a trip round to Bobby's, think about the talks we had and the talks we maybe should have had. I want you to remember me for those full five minutes, no distractions. But the rest of the time is all yours, and I want you to make the most out of every second._

 _The Impala should be at Bobby's, and when you can afford it you can go and pick it up. It's yours. Take good care of it, and if you install an iPod dock I'll come back and haunt you._

 _There's a pretty nurse on my ward called Cathy, and she's coming my way, so I'll make this short._

 _At a risk of it sounding really cheesy, I love you Sammy. You're the best thing that ever happened to me, and don't you forget it. I'm proud of you, Samantha, for standing up for yourself and doing what you want. I guess I'm sorry for not understanding about Stanford, but I can't protect you there. You, dad and the car are the only things I have in this world, and the thought of losing you made me react badly. I'm sorry, and if I could go back and change it I would._

 _When you took your first steps, and when you said your first word, I was there for you. And I was so proud of you. But now it seems like when you walk up the aisle and bring home your new baby for the first time, I won't be there in person. But I will be there, watching over you, looking out for my little brother, even if he is 70 feet tall._

 ** _Dean Winchester_**

Sam didn't realise he was crying until little wet patches started to appear on the letter. He moved it out of the way and dried his tears.

His brother was gone. And he ached for him. He kept expecting to look up and find his pain in the ass big brother standing in front of him, ready to make fun of him for crying like a girl. Sam didn't care. He just wanted his brother back.

He picked up the third letter, wondering briefly what Jess's letter said. Scrawled on the front in too familiar messy handwriting were the words _To Sammy's kid/s, from Uncle Dean._

More tears started to stream down his face. His kids would never get to meet their uncle. His friends would never be able to meet his brother, Jess wouldn't. So much for his ridiculous idea that one day Dean would turn up out of the blue, meeting his friends and sleeping in the spare room of their apartment.

Suddenly Dean's voice appeared in his head, as clear as if Dean was right beside him. _Your five minutes are up, Sammy._ Dean's last wish had been for Sammy to move on, live his life. Well, his last wish was probably that he would survive, but this came at a close second.

He stood up, some feeling returning and pushing out the darkness that had swallowed him whole. He pushed open the door, after placing the letters carefully in a draw.

"Jess?" His voice cracked when she appeared, looking gorgeous despite her red, swollen eyes. Her light blue eyes were brimming with unshed tears.

"Sam." She flew towards him, and he pulled her into his arms, collapsing on the sofa. She buried her head into his chest and cried, and he let himself cry with her. It hurt so much, but it was better than being an empty shell.

Even from beyond the grave, Dean had somehow managed to fix his little brother once again.


	3. A letter from Uncle Dean

This is the last instalment of the story, I'm sorry it took so long. This is the letter that Dean wrote to Sam's kid. I couldn't think of a name for her, so I've left that bit up to you. I can't tell you how grateful I am to you for the follows, favourites and reviews, they're absolutely lovely and have made my day. I hope you enjoy it, I wanted to make this one slightly more upbeat, even though it still ended up pretty sad.

Disclaimer: These beautiful characters are not mine, sadly.

"Can we go out in the Impala? Please? And afterwards can we stop of at the store, they've released a new best of Led Zep album that I really need."

"Do you want it, or need it?" His daughter paused for a second.

"Need it." She was so like Dean sometimes, he just wished his brother could have had the chance to met her. And she would have worshipped Dean, he just knew it.

"Please?" She stuck out her bottom lip, turning on him the lethal puppy dog eyes she seemed to have mastered. Realizing with a pang of loss what he must have been like to his brother when they were younger, he smiled sadly. "Dad? Are you okay? You look kinda sad."

"I'm okay sweetie. Don't worry about me."

"Is it uncle Dean?" Her question took him aback. "When you tell me the stories uncle Dean told you, you always look kinda sad and happy at the same time. And I was thinking…" She trailed off.

Sam swallowed thickly, willing the tears not to fall. He didn't want to cry in front of his daughter.

"Can I just go and get something first? And then we can go for a ride in the Impala."

She nodded and smiled, hugging him tightly. When he got outside she was already sat in the passenger seat, her fingers tapping impatiently. He joined her and she grinned at him.

"What do you want to listen to?" She already had Dean's music collection on her knee. She held each one reverently, knowing how much they meant to her father.

"Can we not put any music on? I need to talk to you properly." They sat in comfortable silence until they came to a country road, where Sam pulled the car to the side of the road. "Sweetie, have I ever told you about my childhood?"

"No, I don't think you have."

"Well, when I was a baby my mom died and my dad took me and Dean out of school and took us all around America. We used to stay in dirty motels and eat the cheapest food on offer, changing schools every couple of weeks. Dad loved us, but he didn't have a very good way of showing it. He'd leave us alone for weeks at a time sometimes, and money would start to run out. So Dean would get a job to try and keep food on the table, tutoring or doing the paper round or something like that. When he couldn't get a way of earning money he wouldn't eat so I wouldn't go hungry." His voice cracked, but he steadied it with a deep breath. "When people used to pick on me he'd defend me, even though it got him in loads of trouble sometimes. Dean pretty much raised me while dad was away, and I looked up to him. Even when he got hurt, he wouldn't let himself cry or show weakness 'cause he didn't want to scare me. Dean was," his breath hitched again, "a hero, and he saved a whole lot of people. One day, while I was at Stanford with your mother, he got killed while he was saving people." This time a tear rolled down his cheek.

"He sent me a letter telling me not to worry, and to get up and live life. That's the thing about Dean, he always thinks about other people. He always puts everyone else above himself."

"He sounds like he loved you a lot." His daughter looked at him, eyes glistening with unshed tears.

"Yeah. Yeah, he did."

"Can you tell me more about him?"

"Um," He racked his brain for something to say. "Dean was the bravest man I ever met. And he was always cracking a joke, trying to make everyone else feel better. He loved this car, it was the closest thing to a home we had. And he loved Led Zep and Kansas and stuff like that, that's his collection of cassettes. All the girls at school loved him, and all the teachers did too, even though they'd never admit it. He followed my dad's orders because he understood what making a mistake could cost you, and he took whatever I said against him for it. And when I walked out half way through a fight, he'd always come and find me. He somehow made everything that little bit better just by being there. It didn't matter that the motel was scruffy and my clothes were a two sizes too big, or that was the fifth school in as many months. 'Cause Dean was there, you know? My big brother was there so everything was gonna be okay."

His daughter's arms suddenly wrapped themselves around him, burying her head into his shoulder.

"He wrote you a letter, you know?" Sam could feel tears sliding down his cheeks, so much for not crying in front of his daughter. "Before he died he wrote a letter to you, even though he never met you. He just didn't want you to think he didn't love you."

Her eyes were the perfect shade of green and blue when she looked up at him. She smiled softly as she took the letter, unfolding it.

 _To Sam future kid/s,_

 _I'm so sorry I never got to meet you. I'm so sorry I never got take you out for ice cream and fill you with sugar so that you were really hyper when you got back home. I'm sorry I never got to take you to the park and tell you embarrassing stories about your dad. I'm sorry I'll never get to drop around at Christmas and sit down with you at dinner, I'm sorry I couldn't take you for a drive and show you some real music. I'm sorry I won't be able to offer to egg the house of the person who broke your heart with you. I'm sorry I won't be there to watch you grow up into an incredible person, which if you're anything like your dad you will be. I'm sorry I wont be there._

 _But I love you, even if you're not even an idea yet. I love you more than any of your other uncles, I swear. I wish I could be there with you, but I'm not. I'm not there, but don't ever forget that I love you so so much (even if you're a total brat), and wherever I am I'll be thinking of you._

 ** _Dean Winchester_**

Sam wrapped his arms around his daughter, and she let her hold him. Then, with a voice so small Sam could barely make it out, she said, "I miss him. I don't even know him but I miss him."

Sam nodded slowly. "Yeah. I miss him too."


End file.
